


The Best Friend & The Brother

by ShirbertofAvonlea



Series: Childhood Chronicles [1]
Category: Anne with an E (TV)
Genre: Gen
Language: English
Status: In-Progress
Published: 2021-01-14
Updated: 2021-01-17
Packaged: 2021-03-18 17:47:23
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 4,692
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28747173
Author URL: https://archiveofourown.org/users/ShirbertofAvonlea/pseuds/ShirbertofAvonlea
Summary: Anne and Diana are best friends. Diana and Gilbert are step-siblings. Anne has a long time crush on Gilbert but Diana just so happens to have a thing against her friends dating her brother. What happens when Gilbert and Anne start secretly dating and try to keep it from Diana?
Relationships: Anne and Gilbert - Relationship, Diana and Jerry, Josie and Jane, Moody and Ruby
Series: Childhood Chronicles [1]
Series URL: https://archiveofourown.org/series/2107533
Comments: 9
Kudos: 8





	1. Chapter 1

It’s the summer before senior year. The teens of Avonlea were all preparing for one last epic summer in high school, one group in particular were getting ready for their annual trip to one of Canada’s biggest amusement parks, Wonderland. Anne and her friends have been taking this trip since the 6th grade when Anne had first moved to Avonlea, this was the first year their parents agreed to let them go by themselves. Just the 10 of them, it wasn’t easy to convince them but they had set the plan in motion last summer when they all agreed having their parents with them that year was kind of a buzzkill for a group of 17 year olds who just wanted to let loose and have fun. So they had decided, as a group, to get jobs and work hard all year so they could save enough money to not only buy the tickets but also for food, gas, new clothes (which apparently were essential for any vacation according to Josie Pye), and they had to rent several rooms at a hotel near the park. Not to mention there were some things they wanted to do outside the park as well so they also saved for that. 

Fortunately they all achieved their goal for the year and were able to convince the overly protective group of parents that they were mature, old enough, and responsible enough to go on their annual trip by themselves. Thank God. Now the time to take the trip has come and all that was left to do was the usual planning. Anne was in charge the supplies needed for the trip there considering it was a 25 hour drive, she had a lot to sort out. 

“Okay, we have water, snacks, soft drinks, extra chargers, first aid kit, emergency cash, spare tires for both cars... what am I missing?” Anne was going through her checklist when she got a call from Diana. “Hey A! How’s the checklist going? Do you need any help?” 

“No, I think I have everything... I just feel like I’m missing something. I have all the essentials like spare tires, first aid kit, snacks, drinks, I even have headlamps for some late night reading but that’s more for me. I can’t figure out what it is I’m missing though.“ 

Diana thought for a moment then said, “Have you packed your own bag yet?” Anne gasped “No! Thank you for reminding me, that would be the one thing I forget.” Diana shook her head through the phone and let out a laugh “That’s what I’m here for. Now hurry up and finish so you can go to sleep. We have a long drive ahead of us tomorrow.” 

The bosom friends said goodnight and ended the call. Anne finished packing her bag and promptly went to sleep but not before setting her alarm for 4 am. “This is going to be the best trip ever!” She thought before falling into a deep sleep. 


	2. Chapter 2

The morning came quicker than Anne had expected but she was ready nonetheless. She got up at the sound of her alarm and made her way to the bathroom. After a quick shower and changing into some clean, comfy clothes she went to the kitchen to silently make herself and Diana a coffee for the road. She made an extra one for Gilbert seeing as he was also stopping at her house first to help put whatever doesn’t fit in Diana’s car in his. Yeah that’s totally why she made him an extra coffee, nothing romantical about her intentions at all. 

She only had to wait about 10 minutes after finishing everything 30 minutes later before Diana and Gilbert showed up. They were nothing if not prompt. Anne said quietly said goodbye to her adoptive parents Matthew and Marilla before heading outside to greet her best friends. “Morning Anne! Are you ready for what’s going to be the most epic summer trip ever!” Diana exclaimed as soon as she saw her bosom friend, she’s always been a morning person. 

Anne smiled and handed her the coffee she made for her before turning to Gilbert. “Hey Gil, I made you one too. Since you have the first driving shift and everything.” He gave her a sweet smile, how could he still look adorable this early in the morning? “Thanks Shirley. Always looking out for me.” She handed him the hot drink and let her fingers linger on his for just a second before giving him a shy smile and turning away. Again, nothing romantical about her intentions. She was just being a good friend. Anyways. 

They packed up the cars and headed to go pick up their other friends. The group had decided they were going to take two cars just because none of them knew how to drive a huge van and it was somewhat cheaper to just take their own cars instead of renting them. In Diana’s car would be mainly the girls like Tillie, Jane, Josie, Ruby, and of course Cole. He was Anne’s other best friend, the three of them used to be a trio up until high school. Nothing bad happened with Cole and Diana they were just never as close with each other as they were with Anne individually. 

So Diana and Anne picked up the girls plus Cole while Gilbert went to pick up Jerry and Moody. They had decided to meet up at the local gas station to grab some extra snacks and fill the cars up with gas, Moody also wanted to try to convince Ruby to ride with him in Gilbert’s car seeing as he has a major crush on her but Gilbert convinced him to wait until later in the trip cause no one wanted to witness him simping over Ruby at 6:30 in the morning. 

Both cars pulled into the gas station and the gang had collectively split up to do whatever they needed to do. Gilbert was filling up his tank when he noticed Anne walking into the store alone. ‘Diana must be in the bathroom’ he thought, he propped the nozzle on the thingy and headed inside hoping to exchange a few words with Anne. 

He caught her in the candy aisle and casually walked towards her, “Little early for Skittles and Twizzlers don’t you think SC?” He was hoping he was coming off as witty and not judgmental. Apparently it worked because Anne met his eyes with a smile. “It’s never too early for the goods Blythe. What’s a better energy source than sugar?” Gilbert was trying to pay attention to her words but all he could think was ‘How does she manage to look like the sun every hour of the day’ in his eyes Anne was glowing. But then again Anne was always glowing whenever Gilbert looked at her, she was just that beautiful to him. Of course he wasn’t going to let her know that, not yet anyways. 

“I mean I guess you’re right, but isn’t that what energy drinks and coffee is for?” He wanted to keep the conversation going for as long as he could seeing as he wouldn’t be able to get his daily Anne fix until they stopped again hours from now. “Yeah, these taste better.” She gave him a smile that almost made him stopped breathing, she seemed to have that effect on him a lot. He wanted to keep going but he could see his friends either at the register or back in the car so he knew he had to wrap it up. 

“If you say so Shirley, good luck with your diabetes.” He joked and turned back to head to the car, but not before grabbing a bag of Skittles himself. He acted like he didn’t hear Anne giggle behind him as he headed up to the register. 10 minutes later they were all back in their selected cars and were ready to hit the road. 


	3. Chapter 3

After about three hours on the road Diana and Gilbert both decided they were too tired to keep driving so they pulled over and switched drivers. In Diana’s car Anne was up next, everyone was still sleeping or groggy so instead of music she just played one of her audio books on low as to not disturb anyone else. In Gilbert’s car Jerry was up next, he was still a little tired from having woken up so early so he took a huge gulp of his energy drink and tried to pump himself up for at least the next three hours. They had been driving for about another hour when both cars started to come alive.

Moody was texting the group chat complaining about how boring it was with just the three of them cause he had no one to talk to because Jerry wanted to focus on the road and Gilbert was peacefully sleeping. Josie and Jane started teasing Ruby about how she should ‘go and keep her man some company’ everyone knew Moody and Ruby had a thing for each other but no one knew why Moody hadn’t made a move yet. “If I go sit in that car I’m not going by myself. I don’t want it to just be me and the boys I need some girl power in there!” Ruby explained. “Me and Jane will go with you. It’s fun watching you and Moody simp and be super awkward yet adorable around each other.” Josie said completely amused, her and Jane had their own thing going too that everyone seemed to see but them. “Thank you, Josie. Even though you’re only doing this to make fun of me.” Josie rolled her eyes at Ruby fondly and let Moody know they’d be switching cars at the next stop.

About an hour and a half later they had stopped to stretch and take bathroom breaks. Ruby, Jane, and Josie followed through on their promise to Moody and made their way to Gilbert’s car. He was ecstatic to say the least. Meanwhile Gilbert made his way over to Diana’s car to talk to none other than Anne. “How’s it going SC? Tired yet or is all that candy helping you stay upright” Anne was still in the drivers seat with the window rolled down so Gilbert could lean on it. “Yup. Like I said nothings a better a energizer than some sugary treats.” Gilbert smiled at her and they continued to talk about nothing until everyone was back in the cars and ready to go. Before he walked away though he said one last thing, “You know my cars open for you too if you decide you wanna switch at some point. It’s gonna be a while before we’re at Wonderland so if you end up getting sick of my sister or something just let me know and I’ll pull over to rescue you.” He had said it jokingly but hoped she knew how serious he was, he really just wanted to spend some time with her without her overprotective best friend, aka his annoying but awesome step sister.

“I could never get tired of Diana,” she laughed “but there wouldn’t be a need to rescue me. I’d be a willing participant in my own kidnapping.” She meant to sound amused but it came out gentler than she had anticipated it to, now they were both just gazing at each other like there was no one else around. Until Cole cleared his throat as if he was signaling that they needed to wrap it up before a certain someone noticed. “Uh, okay. Yeah cool Shirley. Just, um, let me know.” Gilbert, slightly flustered walked back to his car.

Anne was also trying to recover when Cole leaned over and whispered, “You know you guys could try a little harder to act like you’re not totally in love with each other.” Anne looked at him with wide eyes and then looked to Diana to see if she had heard but she had her headphones in. “I am not in love with Gilbert. And he’s not in love with me, he was just being friendly.” Cole looked unimpressed, “If I had a friend look at me like that I’d think they were in love with me. Just saying.” Anne glared at him, “Shut up Cole.” She said as he leaned back in his seat laughing.

Diana, finally looked up from her phone with a smile and suggested they play the road trip playlist she made specifically for this trip. Anne smiled at her best friend, “Duh! That’s literally its an entire purpose.” Diana plugged in her phone and took over the aux. The first song that played made Tillie pop up from where she was knocked out in the backseat, “I love this song! Turn it up!” Anne cranked up the music and the four of them jammed out, it was finally starting to feel like the epic road trip they had been so excited for over the last year. Anne, although was actively singing along, couldn’t help but hear Cole’s words in the back of her head. ‘If a friend looked at me like that I’d think they were in love with me.’ She couldn’t help but wonder, is it possible her silly childhood crush on her best friends brother wasn’t unrequited after all?


	4. Chapter 4

Jerry was still behind the wheel in Gilbert’s car, he was trying to find a way to subtly ask him if he planned to make moves on Anne during this trip without the others hearing. He quickly realized they were all too wrapped up in themselves to even pay attention to what he was saying at the moment. Lots of flirting going on in the backseat. So, Jerry turned to Gilbert.

“Hey, are you gonna try to make a move on Anne this time or am I gonna have to spend another year watching you pine after her?” Gilbert scoffed, “I do not _pine_ after Anne. Who even uses words like that anymore?” 

“Anne.” Jerry deadpanned. Gilbert rolled his eyes and shifted in his seat, “If you must know, yes, I have a plan. And I need your help.” Jerry was skeptical but was pretty much open to anything considering he’s been waiting for these two to get together for years now. “What can I do for ya?” 

“So I know you’ve got a thing for my sister,” Jerry tried to object, “I do not have-“ “You’ve got a big ass crush on my sister, dude. It’s fine I’ve processed it, accepted it, now I’m going to use it to my advantage.” Jerry conceded, “What do you need me to do?” 

“Anne and Diana are always joined at the hip anytime we take this trip right, so I need you to distract my sister by flirting with her so I can get closer to Anne.” Jerry blinked, once, twice, then said “Does Diana even like me like that?” Gilbert laughed and patted Jerry on the arm, “Of course she does man. You’re literally all she talks about in her diary,” “You read her diary?” Gilbert’s eyes widened but he quickly made his face as neutral as possible. “Not the point. The point is you and my sister have a thing for each other so I don’t see the harm in using that to get closer to Anne. In the end we’d both, hopefully, be with the person we wanna be with you know?” 

Jerry wanted to say no, but he couldn’t deny the fact that it actually might be a good plan. Kinda screwed up and manipulative but still... it could work. Plus he’d get a chance to finally sweet talk Diana without worrying whether or not Gilbert would approve. Looks like he’s on board. 

“Alright, I’m in.” Gilbert fist pumped in the air, “Yes! Okay so first order of business, get Anne to switch cars _without_ Diana.” Jerry sighed deeply, “You know that’s not gonna be easy, they’re like conjoined twins sometimes I swear.” Now it was Gilbert's turn to sigh, “I know, that’s what you’re here for. Help me come up with a plan.”

***

The jam session had died down about 10 miles ago, now the remaining 4 in the car were either sleeping or on their phone. Diana was talking to Anne to try to keep her energy up as she was still driving, “Do you think I’ll finally have a shot with Jerry this year? Like I know it’s gonna be senior year and we should focus on having fun but I kinda wanna be in a relationship for my last year of high school you know?” Anne knew exactly how she felt. “Of course you’ll have a shot with Jerry! It’s so obvious he likes you I just can’t figure out why he hasn’t made a move yet.” Diana shifted in her seat, “You really think so? I mean I always figured he looked at me like I’m just Gilbert’s sister. Like how Gilbert sees you as like, his sister’s best friend you know.” Ouch. That stung. “Well, you never know unless you try.” Anne tried to mask her hurt feelings by suggesting they turn the music back up. 

She didn’t really feel like driving anymore so she told Diana to text the group chat and let them know to pullover at the next gas station. As soon as Anne pulled in and parked the car she got out and speed walked to the bathroom. She wasn’t insanely hurt or heartbroken or anything like that, she just needed a breather. “Okay Anne, get it together.” She told herself before taking a deep breath and splashing water on her face. Once she felt better she walked out the bathroom just to be greeted by Cole. 

“Hey” she said, “I heard what Diana said, about Gilbert only seeing you as his sister’s friend. You know that’s not true right? Like it couldn’t be farther from the truth.” Anne shook her head, disagreeing, “I don’t know Cole. I feel like if he saw me as more than that he would’ve said something by now.” Cole stared at her blankly, “You really think he would’ve made a move when Diana has literally been a cock block for you two since the 6th grade? He hasn’t made a move because he hasn’t had the chance Anne. Trust me. You see a lot when you’re not directly in the eye of the tornado.” 

Anne laughed and shook her head, still not convinced about what Cole was saying “I’ll see you back at the car.” She walked back to where the cars were parked and was greeted by an enthusiastic Diana, “Oh my gosh Anne! Jerry wants to switch cars something about wanting to spend time with me? I don’t know but would you mind if he joined us?” Diana was talking a mile a minute, clearly excited and nervous about spending time with Jerry. “Of course I don’t mind! This is your shot he’s finally making a move! Go for it!” 

They walked back to the cars together where they saw Gilbert pumping gas into his. He motioned for Anne to come over to him, she was about to turn to Diana to tell her she’ll be right back but she was already completely enamored by her crush. She headed over to Gilbert, still feeling a little shy since Diana made that comment but that quickly went away when he said, “So, since my best friend has abandoned me to go hang with my sister I was thinking we could make a trade. Best friend for best friend kinda thing. What do you say?” Anne didn’t know what to say. Was it possible Cole was right? Did Gilbert actually _want_ to spend time with her? 

“I mean, I guess it’s only fair...” The smile on his face said it all. Okay, maybe he doesn’t see her as just a friend, or rather, just his sisters friend. “Cool, I’ll save you the front seat.” Anne felt hot, she hoped, no _prayed_ , that her face wasn’t as red as her hair. She walked back to Diana’s car and quietly tapped her shoulder seeing as she was deep in flirt mode with Jerry, “Hey, so I’m gonna ride in Gilbert’s car for a while. Give you two a chance to talk without you worrying about having to give me any attention.” She laughed like it was a joke but really she was just nervous. “Are you sure? You know Gilbert can be a pain in the ass.” 

“I’m sure.” Is all Anne could say as she grabbed some of her stuff to take over to Gilbert’s car. “Okay, just text me if you feel like you can’t take it anymore. I know I can only handle so much Gilbert.” They shared a laugh and Anne headed over to Gilbert avoiding Cole’s knowing stare. She hopped in the passenger seat, suddenly more nervous than she was before. He spoke first, “Mission accomplished.” Anne turned to him, “Huh?” 

“I said I was gonna kidnap you, and I did. So mission accomplished.” Anne laughed and shook her head, “I don’t think you can count it as a kidnapping if I came willingly.” “Still, glad I could convince you to come. I actually enjoy your company.” Gilbert said with the shyest smile Anne has ever seen on his boyish face. “Yeah?” He reached over and grabbed her hand, “Yeah.” Great now they were both smiling like idiots. They pulled out of the parking lot and got back on the road, Anne couldn’t stop staring at their hands intertwined like that. It made her heart swell and her mind wonder, could this actually be the start of something new? 


	5. Chapter 5

The gang had been driving about 16 hours at this point, taking frequent stops to use the bathroom, stretch, fuel up, and switch drivers. In Diana’s car her and Jerry had been so focused on each other Diana seemingly forgot about Anne being ‘stuck’ in the other car with her brother. She shot her a text asking how she was doing but it was late into the night so she didn’t expect a response. 

Meanwhile in Gilbert’s car, everyone was asleep aside from Anne and Gilbert of course. Ruby had fallen asleep on Moody’s lap while he played with her hair until he fell asleep himself, Jane and Josie had somehow found a comfortable way to cuddle each other while being sprawled out in the last row of the car. The rotation of driving shifts landed on Gilbert again but he didn’t mind seeing as Anne was awake too, he could feel her tired gaze on him and he tried not to smile. Anne liked watching him drive, there was something kind of romantic about how the moon was shining on him through the window, how the radio was softly playing in the background, and not to mention how late it was. She could almost imagine that they were the only two there and they were just enjoying each other’s company on a late night drive. Until Moody started slightly snoring. 

The sudden sound was enough to make Anne jump in her seat, causing Gilbert to softly chuckle. “Shut up” she said quietly so she wouldn’t wake the others. They spoke in low voices, “Did Moody scare you?” Gilbert asked amused. “It was just sudden that’s all.” 

“Are you gonna go back to gazing at me or has the moment passed?” Anne felt her cheeks get hot, “I wasn’t gazing at you Blythe.” She said determined to hold her ground, “Sureee SC. It’s okay, I don’t mind. I know how handsome I can be.” Anne almost snorted

”If you must know I wasn’t staring at you, I was looking at the moon. It’s really pretty tonight.” She tried to lie but it quickly backfired, “The moon is on your side.” Damn you Gilbert Blythe. Anne, more embarrassed than she was initially, shifted her entire body to face the other direction. Gilbert laughed, “Come on Anne, I was only teasing. Turn back around.” 

“Why” she mumbled. “Because the moon isn’t the only thing that’s pretty tonight...” he admitted. Bold as it was Gilbert almost immediately regretted saying it when she didn’t automatically turn around. Now it was his turn for his face to get hot, but sure enough Anne slowly faced her body back towards Gilbert, trying to hide her blush. “There she is.” He gave her that smile, that smile that turned her into a puddle of emotions every time he directed it towards her. She wasn’t sure what else to say so she just smiled back and let herself drift into a deep sleep. 

When Gilbert looked back at her after watching the road, he didn’t ignore the tug on his heart when he saw she fell asleep with a soft smile he could only assume was meant for him. 

***

When the sun had rose so did everyone else. They only had about 5 hours left of their drive so they decided to stop at a diner to eat and freshen up in the bathrooms. Diana grabbed Anne as soon as the stepped out of the cars, “I’m so sorry” she said in the most sincere tone. “For what?” Anne had no idea what Diana was apologizing for. “For leaving you with my obnoxious excuse of a brother. On a scale from 1-10 how bad was it, be honest.” Anne playfully rolled her eyes, she really had no idea why Diana thought Gilbert was so terrible. Maybe it’s a sibling thing.

“He wasn’t bad at all, it was kinda fun if I’m being honest.” She wasn’t. It was tons of fun and she had butterflies pretty much the whole time, but no way was she going to say that out loud. “He’s always so different around you, I swear. It’s like he’s trying to hide his obnoxiousness just so that I look crazy.” Diana sighed, slightly annoyed. That’s when Cole walked up, “Or maybe he has a thing for Anne.” He said wiggling his eyebrows between the two girls.

Anne’s eyes were so wide Cole thought they might pop out of her head, meanwhile Diana said, “Yeah, right. My brother and Anne? Gilbert and Anne together? Real funny Cole.” Diana had laughed it off but Cole persisted, “Why is that funny Diana? Is our lovely friend Anne here not good enough for your brother or something?” Anne could tell he was just trying to get an honest answer out of her but she really didn’t want to hear it right now, reasonable or not. “What? Cole how could you say that?” Diana looked genuinely horrified at Cole’s accusations. “Okay! You know what it’s way too early for this and I’m starving, let’s go inside.” Anne said hurrying the two inside the diner.

Later on when they were all done with breakfast and loading back up in the cars Anne pulled Cole aside. “What the the actual hell was that?” She said through gritted teeth, “What? I just wanted to know why she thought the idea of you and Gilbert together was so hilarious.” He said innocently, as if he hadn’t just caused tension between the girls. “I don’t want to know what she thinks about it because it’s not happening. Not ever. So just drop it and never bring it up again, okay?” Cole had opened his mouth to say more but Anne had already walked away to Gilbert’s car.

“Jane, it’s your turn to drive. I’ll take your seat in the back.” As much as Anne didn’t want to be around Cole or Diana for a while, she also didn’t want to be around Gilbert either. Everything just felt too weird now, she needed a couple hours to think and the backseat was the best privacy she was going to get at the moment. She noticed Gilbert had a disappointed look on his face as she climbed in the back. She didn’t say anything. She just put on her headphones and tried to drown everything out. At least for the next few hours.

**Author's Note:**

> Hi! If you’re coming from my Twitter Au I hope you enjoy this more detailed version of my story! If you’re new and just finding this I hope it’s also a good read for you :) let me know your thoughts in the comments!


End file.
